The Chicago Bears changed their fortunes in 2025 by overhauling the offensive line, but the football gods have been as cruel this offseason as they were kind last spring with regards to that crucial unit.
Chicago saw second-round rookie Ozzy Trapilo, who elevated into the starting role at left tackle, suffer a torn patellar tendon in Round 1 of the playoffs, which will likely cost him most of next season. Not long after, Pro Bowl center Drew Dalman unexpectedly retired one year into a three-season contract amid his prime.
Head coach Ben Johnson has a potential superstar at quarterback in Caleb Williams, but Johnson changed the offense by turning it into one of the top rushing attacks in the NFL last season. The Bears must bridge the gap back to Trapilo’s health by filling the left tackle spot with a player who can both support the run-first offense Johnson has implemented and also protect Williams’ blindside.
Chicago could not find that player at value based on its positioning in the draft last weekend, but one possible option remains available in free agency: former Detroit Lions starter Taylor Decker.
Taylor Decker, Ben Johnson Spent Years Together With Lions
GettyFormer Detroit Lions left tackle Taylor Decker (right).
Decker started 10 years for the Lions, earning Pro Bowl honors in 2024. However, he asked the team to cut him loose this offseason just one year into his $60 million contract, and Detroit obliged.
Tyler Sullivan of CBS Sports recently dubbed Chicago as the top fit for Decker, who remains a free agent.
“Given that prior relationship, Decker could be an insurance option at left tackle for Johnson’s Bears,” Sullivan wrote. “The Bears did sign Jedrick Wills Jr. earlier this offseason, but that shouldn’t preclude them from possibly adding Decker to compete for the job.”
Chicago also brought back Braxton Jones on a one-year deal, who lost the starting role at left tackle to 2024 undrafted rookie Theo Benedet last season. Benedet, who is also still on the roster, ultimately surrendered the gig to Trapilo.
Bears Don’t Have Great Options at Left Tackle Next Season
GettyLeft tackle Taylor Decker, formerly of the Detroit Lions.
Injuries, return timelines, salaries and the team’s recent success have stuck the Bears with something of a conundrum at left tackle.
On the one hand, Trapilo looks like a viable starting option at one of the game’s premier positions on a second-round contract that runs through 2028. Paying a player like Decker, who Spotrac projects will command a two-year deal worth approximately $42.65 million, robs Chicago of the value it found in Trapilo — and he should be back, and fully healthy, by the 2026 season’s end.
But the Bears have their momentum and continued progress to consider, not to mention the health and well-being of Williams, the former No. 1 overall pick in 2024 and the franchise quarterback with top-of-the-league upside.
Chicago couldn’t secure a starting tackle early in the draft due to its Round 1 position, and ready-made options on the left side were somewhere between scarce and non-existent in this year’s class anyway.
Relying on Jones, Benedet and Wills, the latter of whom was a first-round bust of the Cleveland Browns and sat out all last season due to injury, provides the Bears with a patchwork a solution, but that path forward represents considerable risk in multiple forms.
Decker is in his early 30s and his play is trending in the wrong direction based on advanced metrics. He’s also the best option still available in free agency and considerably better than anyone healthy and currently on Chicago’s roster.
Bears Premier Fit for $60 Million Pro Bowler, Recent Lions Castoff